CN103597053A - Novel compounds and organic electronic device using same - Google Patents

Novel compounds and organic electronic device using same Download PDF

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CN103597053A
CN103597053A CN201280029168.4A CN201280029168A CN103597053A CN 103597053 A CN103597053 A CN 103597053A CN 201280029168 A CN201280029168 A CN 201280029168A CN 103597053 A CN103597053 A CN 103597053A
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CN103597053B (en
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申昌桓
金公谦
李东勋
张俊起
千民承
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LG Chem Ltd
LG Corp
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Abstract

The present invention provides novel compounds and an organic electronic device using the same. The compounds according to the present invention can perform the role of light-emitting materials such as hole injection, hole transport, electron injection and transport, and the like, in organic electronic devices, including organic light-emitting devices, and the organic electronic devices according to the present invention show excellent characteristics for efficiency, driving voltage and lifespan.

Description

The organic electronic devices of new compound and this compound of use
[technical field]
The application requires the right of priority of No. 10-2011-0056777th, korean patent application that in June, 2011,13 Koran Office submitted to, and its whole disclosures are included this specification sheets by reference in.
The present invention relates to new compound and use the organic electronic devices of this compound.
[background technology]
In this manual, organic electronic devices is for using the electron device of organic semiconductor material, and need to be between electrode and organic semiconductor material exchange hole and/or electronics.Organic electronic devices can roughly be divided into following two classes according to operation logic.The first kind, a kind of electron device, wherein exciton is formed by the photon that flows into device from external light source at organic material layer, and described exciton is separated into electronics and hole, and described electronics and hole are transferred to respectively other electrodes and are used as current source (voltage source).Equations of The Second Kind, a kind of electron device, wherein by two or more electrode application voltage or electric current by hole and/or electronic injection organic semiconductor material layer, form interface with electrode, and this equipment moves by injected electrons and hole.
The example of organic electronic devices comprises organic luminescent device, organic solar batteries, organic light-guide (OPC) drum, organic transistor etc., and needs electrons injecting material, electrons to extract material, electrons transport material or luminescent material to drive all these devices.Below, will mainly describe organic luminescent device in detail.Yet in organic electronic devices, all electrons injecting materials, electrons are extracted all operations of the principle based on similar of material, electrons transport material and luminescent material.
Generally speaking, organic light emission phenomenon refers to by using the phenomenon that organic materials is luminous energy by electric energy conversion.Organic luminescent device by organic light emission phenomenon has the structure that generally includes anode, negative electrode and be placed in organic issuance of materials layer therebetween.Herein, organic material layer has the multilayered structure that comprises differing materials conventionally, to improve organic light-emitting device efficiency and stability, for example, can comprise hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc.In organic light-emitting device structure, if apply voltage between two electrodes, hole is from anode injection organic material layer and electronics from negative electrode injection organic material layer, when injected holes and electrode meet each other, will form exciton, and will send light when exciton is down to ground state.Known this organic luminescent device has following performance: such as self-luminosity, high brightness, high-level efficiency, low driving voltage, wide visual angle, high-contrast, high-speed response etc.
In organic luminescent device, the material that is used as organic material layer can be divided into luminescent material and charge transfer material according to its function, for example, and hole-injecting material, hole mobile material, electron transport material, electron injection material etc.The example of luminescent material comprises blue-light emitting material, green luminescent material and the material and need to realize the Yellow light-emitting low temperature material of better natural colour and send out orange luminescent material according to glow color of glowing.In addition, in order to improve colour purity and to improve by the luminous efficiency of transmission ofenergy, can be by main body/adulterate body (host/dopant) system as luminescent material.In principle, by a small amount of energy band broad gap adulterate body narrower than the main body of main composition luminescent layer and that have an excellent luminous efficiency is mixed with luminescent layer, the exciton producing in main body is transferred to adulterate body and has high efficiency light to send.Now, because the wavelength of main body is shifted to the wavelength bandwidth of adulterate body, so according to the kind of adulterate body used, obtain the light of required wavelength.
In order fully to represent above-mentioned organic light-emitting device excellent properties, form the material of the organic material layer in device, needs such as hole-injecting material, hole transport material, luminescent material, electron transport material, electron injection material are mainly by stablizing and effective materials for support, but for organic light-emitting device stable and effectively organic materials layer material not yet realize abundant exploitation.Therefore, still there is the lasting demand of exploitation novel material.
[summary of the invention]
[technical problem]
The present inventor has now found that a kind of compound with new structure.In addition, contriver also finds the following fact: when passing through to use the organic material layer of this new compound formation organic electronic devices, can obtain for example device efficiency raising, driving voltage reduction, stability raising texts.
Therefore, the object of the present invention is to provide the organic electronic devices of a kind of new compound and this new compound of use.
[technical scheme]
The invention provides a kind of compound being represented by following formula 1.
[formula 1]
Figure BDA0000437024830000031
Wherein
At least one in R1 to R9 represented by following formula 2 and all the other are hydrogen; Deuterium; Halogen group; Itrile group; Nitro; Hydroxyl; Replace or unsubstituted cycloalkyl; Replace or unsubstituted alkoxyl group; Replace or unsubstituted aryloxy; Replace or unsubstituted alkyl sulfenyl (alkylthioxy group); Replace or unsubstituted artyl sulfo; Replace or unsubstituted alkyl sulphinyl (alkylsulfoxy group); Replace or unsubstituted aryl sulfonyl kia; Replace or unsubstituted thiazolinyl; Replace or unsubstituted silyl; Replace or unsubstituted boryl; Replace or unsubstituted alkylamino; Replace or unsubstituted arylalkylamino; Replace or unsubstituted virtue amino; Replace or unsubstituted assorted virtue amino; Replace or unsubstituted aryl; Replace or unsubstituted fluorenyl; Replace or unsubstituted carbazyl; Or replacement or the unsubstituted heterocyclic radical containing one or more N, O and S atom; And
[formula 2]
Figure BDA0000437024830000032
L is direct bond (direct bond); Replace or unsubstituted arylidene; Or replacement or the unsubstituted inferior heteroaryl containing one or more N, O and S atom,
Ar1 and Ar2 are independently of one another for replacing or unsubstituted aryl; Or replacement or the unsubstituted heterocyclic radical containing one or more N, O and S atom,
A is O, S or Se.
In addition, the invention provides a kind of organic electronic devices, it comprises that the first electrode, the second electrode and one or more layers are placed in the organic material layer between described the first electrode and the second electrode, and wherein said one or more layers organic material layer comprises the compound being represented by formula 1.
[beneficial effect]
New compound of the present invention can be used as by introducing multiple substituting group etc. the material of the organic material layer that comprises organic light-emitting device organic electronic devices.The compound that use is represented by formula 1 of the present invention shows excellent performance as the organic light-emitting device organic electronic devices that comprises of the material of organic material layer at aspects such as efficiency, driving voltage, life-spans.
[accompanying drawing explanation]
Fig. 1 illustrates a kind of structure of organic light-emitting device, and wherein, anode 102, luminescent layer 105 and negative electrode 107 stack gradually in substrate 101.
Fig. 2 illustrates a kind of structure of organic light-emitting device, and wherein, anode 102, hole injection/hole transport and luminescent layer 105, electron transfer layer 106 and negative electrode 107 stack gradually in substrate 101.
Fig. 3 illustrates a kind of structure of organic light-emitting device, and wherein, substrate 101, anode 102, hole injection layer 103, hole transport and luminescent layer 105, electron transfer layer 106 and negative electrode 107 stack gradually.
Fig. 4 illustrates a kind of structure of organic light-emitting device, and wherein, substrate 101, anode 102, hole injection layer 103, hole transmission layer 104, electric transmission and luminescent layer 105 and negative electrode 107 stack gradually.
[preferred forms]
Below, the present invention will be described in more detail.
New compound of the present invention is represented by formula 1.
In formula 1, R5 can be represented by formula 2, but be not limited to this.
In compound of the present invention, the substituting group in formula 1 will be described below in more detail.
Alkyl can be straight or branched, and does not specifically limit the number of its carbon atom, but preferably 1 to 12.Its specific examples comprises methyl, ethyl, propyl group, sec.-propyl, butyl, the tertiary butyl, amyl group, hexyl, heptyl etc., but is not limited to this.
Thiazolinyl can be straight or branched, and does not specifically limit the number of its carbon atom, but preferably 2 to 12.Its specific examples comprises thiazolinyl such as the stilbenyl (stylbenyl) that is connected with aryl, styryl (styrenyl) etc., but is not limited to this.
Alkynyl can be straight or branched, and does not specifically limit the number of its carbon atom, but preferably 2 to 12.Its specific examples comprises ethynyl, proyl etc., but is not limited to this.
Cycloalkyl is preferably the group with 3 to 12 carbon atoms, and it does not produce sterically hindered.Its specific examples comprises cyclopentyl, cyclohexyl etc., but is not limited to this.
Cycloalkenyl group preferably has 3 to 12 carbon atoms, and its more specifically example be included in ring compound having in five-ring or six-ring vinylidene etc., but be not limited to this.
Alkoxyl group preferably has 1 to 12 carbon atom, and its more specifically example comprise methoxyl group, oxyethyl group, isopropoxy etc., but be not limited to this.
Aryloxy preferably has 6 to 20 carbon atoms, and its more specifically example comprise phenoxy group, cyclohexyloxy, naphthyloxy, biphenylyloxy etc., but be not limited to this.
Alkylamino preferably has 1 to 30 carbon atom, and its more specifically example comprise methylamino-, dimethylamino, ethylamino, diethylin etc., but be not limited to this.
Virtue amino preferably has 5 to 30 carbon atoms, and example comprises that phenyl amino, naphthyl are amino, xenyl is amino, anthryl is amino more specifically, 3-methyl-phenyl amino, 4-methyl-naphthyl amino, 2-methyl-xenyl amino, 9-methyl-anthryl amino, diphenyl amino, phenyl napthyl amino, xylyl are amino for it, phenyltolyl base amino, triphenyl are amino etc., but is not limited to this.
Aryl can be monocycle or many rings, and does not specifically limit the number of its carbon atom, but preferably 6 to 40.The example of monocyclic aryl comprises phenyl, xenyl, terphenyl (terphenyl), Stilbene base etc., and the example of polyaromatic comprise naphthyl, anthryl, phenanthryl, pyrenyl, perylene base,
Figure BDA0000437024830000052
base, fluorenyl etc., but be not limited to this.
Heteroaryl is for comprising O, N, S or P as heteroatomic cyclic group, and specifically do not limit the number of carbon atom, but preferably 3 to 30.The example of heterocyclic group comprises carbazyl, thienyl, furyl, pyrryl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, pyridazinyl, quinolyl, isoquinolyl, acridyl etc., and preferably there is the compound of following structural formula, but be not limited to this.
Figure BDA0000437024830000051
Figure BDA0000437024830000061
The example of halogen group comprises fluorine, chlorine, bromine, iodine etc., but is not limited to this.
The specific examples of arylidene comprises phenylene, biphenylene, naphthylidene, sub-binaphthylyl, anthrylene, fluorenylidene, Asia base (chrysenylene), phenanthrylene etc., but be not limited to this.
The example of Heterocyclylalkyl comprises containing the heteroatoms cyclic group of N, S or O for example.
In addition, as used herein, term " replacement or not replacement " means group and is replaced by one or more substituting groups, described substituting group is selected from deuterium, halogen, alkyl, thiazolinyl, alkoxyl group, silyl, aryl alkenyl, aryl, heteroaryl, carbazyl, arylamino, by aryl, is replaced or unsubstituted fluorenyl and itrile group, or does not have substituting group.
R1 to R9 in formula 1, L, Ar1, Ar2 and A can further be replaced by other substituting groups, described other substituent examples comprise halogen group, alkyl, thiazolinyl, alkoxyl group, silyl, aryl alkenyl, aryl, heteroaryl, carbazyl, arylamino, by aryl, are replaced or unsubstituted fluorenyl, itrile group etc., but are not limited to this.
The preferred specific examples of the compound that formula 1 is represented comprises following compound, but is not limited to this.
Figure BDA0000437024830000063
Figure BDA0000437024830000071
Figure BDA0000437024830000081
Figure BDA0000437024830000091
Below, will the preparation method of the compound being represented by formula 1 be described.
The compound being represented by formula 1 can be by using ordinary method known in the art to prepare, such as using the preparations such as condensation reaction and Suzuki linked reaction.
By introducing multiple substituting group to the represented core texture of described formula, the compound being represented by formula 1 can have the characteristic that is suitable for use as the organic material layer using in organic luminescent device.The compound being represented by formula 1 can show the characteristic being used in the arbitrary layer of organic light-emitting device, but particularly can show following characteristic.
Introduce to replace or the compound of unsubstituted arylamino is suitable for as luminescent layer and hole is injected and the material of hole transmission layer, and the compound of introducing the heterocyclic radical that contains N is suitable for the material as electron injecting layer, electron transfer layer and hole blocking layer.
Conjugate length and the band gap of compound are closely related.Particularly, band gap reduces along with the increase of compound conjugate length.As mentioned above, by the core of the represented compound of formula 1, comprise limited conjugation, and therefore there is little band gap to the characteristic of large band gap.
In addition the compound that, has the natural characteristics of introduced substituted radical can synthesize by multiple substituting group is introduced to above-mentioned core texture.For example, hole injection layer material and hole transport layer material used in organic light-emitting device manufacturing processed have the energy level being enough to along HOMO transporting holes, and can become and can have the compound that is enough to stop the energy level moving that electronics flows from luminescent layer along LUMO.Especially, the core texture of the compounds of this invention shows the stability to electronics, therefore, contributes to improve device time limit of service.Can prepare by introducing substituting group and make the derivative for luminescent layer and electron transfer layer, thereby make various adulterate body, the adulterate bodies based on aryl based on arylamines and the adulterate body that contains metal etc. there is suitable band gap.
In addition, by introduce multiple substituting group to core texture, can accurately control band gap, and improve the performance of the interface between organic materials, make thus described material can be used for every field.
Meanwhile, the compound being represented by formula 1 has high second-order transition temperature (Tg), therefore it has excellent thermostability.The raising of thermostability is to provide to a device important factor that drives stability.
In addition, organic electronic devices of the present invention is to comprise that the first electrode, the second electrode and one or more layers are placed in the organic electronic devices of the organic material layer between described the first electrode and the second electrode, and described one or more layers organic material layer comprises the compound being represented by formula 1.
Organic electronic devices of the present invention can be manufactured by the conventional manufacture method of organic electronic devices and material, and difference is, one or more layers organic material layer is by being used above-claimed cpd to form.
The compound of formula 1 can be by being used vacuum deposition method and solution coat method to form organic material layer in the manufacturing processed of organic electronic devices.Herein, solution coat method means spin-coating method, dip coating, ink jet printing method, silk screen print method, spray method, rolling method etc., but is not limited to this.
The organic material layer of organic electronic devices of the present invention can be comprised of single layer structure, also can be formed by multilayered structure, and in multilayered structure, stacking two-layer or multilayer organic material layer.For example, organic electronic devices of the present invention can have following structure: comprise that hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc. are as organic material layer.Yet the structure of organic electronic devices is not limited to this, and can comprise the still less organic material layer of the number of plies.
Therefore,, in organic electronic devices of the present invention, organic material layer can comprise that one or more layers hole injection layer, hole transmission layer and one deck inject simultaneously and the layer of transporting holes and one or more layers can comprise the layer of the compound being represented by formula 1.
In addition, organic material layer can comprise one deck luminescent layer, and described luminescent layer can comprise the compound being represented by formula 1.
In addition, organic material layer can comprise that one or more layers electron transfer layer, electron injecting layer and one deck transmit simultaneously and inject layer and one or more layers layer that can comprise the compound that represented by formula 1 of electronics.
In having the organic material layer of multilayered structure, the compound of formula 1 can be included in luminescent layer, injection/transporting holes and luminous layer, transporting holes and luminous layer or transmission electronic and luminous layer simultaneously simultaneously simultaneously.
For example, organic light-emitting device structure of the present invention has the identical structure of structure as shown in Fig. 1 to 4, but is not limited to this.
Fig. 1 illustrates a kind of structure of organic light-emitting device, and wherein, anode 102, luminescent layer 105 and negative electrode 107 stack gradually in substrate 101.In described structure, the compound of formula 1 can be included in luminescent layer 105.
Fig. 2 illustrates a kind of structure of organic light-emitting device, and wherein, anode 102, hole injection/hole transport and luminescent layer 105, electron transfer layer 106 and negative electrode 107 stack gradually in substrate 101.In described structure, the compound of formula 1 can be included in hole injection/hole transport and luminescent layer 105.
Fig. 3 illustrates a kind of structure of organic light-emitting device, and wherein, substrate 101, anode 102, hole injection layer 103, hole transport and luminescent layer 105, electron transfer layer 106 and negative electrode 107 stack gradually.In described structure, the compound of formula 1 can be included in hole transport and luminescent layer 105.
Fig. 4 illustrates a kind of structure of organic light-emitting device, and wherein, substrate 101, anode 102, hole injection layer 103, hole transmission layer 104, electric transmission and luminescent layer 105 and negative electrode 107 stack gradually.In described structure, the compound of formula 1 can be included in electric transmission and luminescent layer 105.
In organic electronic devices of the present invention, the compound being represented by formula 1 is more preferably included in electron transfer layer, transmits and inject simultaneously layer or the luminescent layer of electronics.
For example, organic luminescent device of the present invention can be manufactured in the following manner: by physical vapor deposition (PVD) rule, as sputtering method or electron-beam vapor deposition method make to have the metal of electroconductibility or metal oxide or its alloy deposition, form anode in substrate, in substrate, form the organic material layer comprise hole injection layer, hole transmission layer, luminescent layer and electron transfer layer, then by the deposition of material that can be used as negative electrode thereon.Except these methods, organic luminescent device can be by making cathode material, organic material layer and anode material be deposited in substrate and manufacture successively.
Organic material layer can be multilayered structure, and described multilayered structure comprises hole injection layer, hole transmission layer, luminescent layer, electron transfer layer etc., also can be single layer structure, but is not limited to this.In addition, having the still less organic material layer of the number of plies can use multiple polymers material by preparations such as solvent method such as the spin-coating method except sedimentation, dip coating, spread coating, silk screen print method, ink jet printing method, thermal shift assay.
For anode material, preferably conventionally use the material with high work content, to impel hole injection organic material layer.The specific examples that can be used for anode material of the present invention comprises metal, for example vanadium, chromium, copper, zinc and gold or its alloy; Metal oxide, for example zinc oxide, Indium sesquioxide, tin indium oxide (ITO) and indium zinc oxide (IZO); The binding substances of metal and oxide compound, for example ZnO:Al or SnO 2: Sb; And conductive polymers, for example poly-(3-methyl compound), poly-[3,4-(ethylidene-1,2-dioxy base) compound] (PEDT), polypyrrole, polyaniline etc., but be not limited to this.
For cathode material, preferably conventionally use the material with low work content, to impel electronic injection organic material layer.The specific examples of cathode material comprises metal, for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead, or its alloy; Sandwich is LiF/Al or LiO for example 2/ Al etc., but be not limited to this.
Hole-injecting material for impelling the material injecting from the hole of anode under low voltage.The highest occupied molecular orbital(HOMO) of hole-injecting material (HOMO) is preferably between the work content of anode material with around between the HOMO of organic material layer.The specific examples of hole-injecting material comprises that metalloporphyrin, oligothiophene, the organic materials based on arylamine, the organic materials based on six nitrile six azepine benzophenanthrenes (hexanitrile hexaazatriphenylene), the organic materials based on quinacridone, base are in organic materials, anthraquinone and the conductive polymers based on polyaniline of perylene and the conductive polymers based on polyacetylene compound etc., but is not limited to this.
Hole mobile material is the material that hole mobility is high suitably, and it can receive from the hole of anode or hole injection layer and transmit it to luminescent layer.Its concrete example comprises organic materials, conductive polymers based on arylamine, has the segmented copolymer of conjugate moiety and non-conjugated part etc., but is not limited to this.
Luminescent material is for by receiving and recombinating respectively from the hole of hole transmission layer and material that can be luminous in visible region from electron transfer layer electronics, and preferably fluorescence and phosphorescence had the material of high-quantum efficiency.Its concrete example comprises 8-hydroxyl-quinoline aluminum complex compound (Alq 3); Compound based on carbazole; Dimerization distyryl compound; BAlq; 10-hydroxy benzo quinoline-metallic compound; Compound based on benzoxazole, the compound based on benzothiazole and the compound based on benzoglyoxaline; Based on poly-(to phenylene vinylidene) polymkeric substance (PPV); Spirocyclic compound; Poly-fluorenes, rubrene (rubrene) etc., but be not limited to this.
Electron transport material is the material that electronic mobility is high suitably, and it can receive from the electronics of negative electrode and transmit it to luminescent layer.Its concrete example comprise oxine Al complex compound, comprise Alq 3complex compound, organic group compound, flavonol metal complex etc., but be not limited to this.
Organic luminescent device of the present invention can be top light emitting-type, end light emitting-type or dual-side emissive type according to used material.
Compound of the present invention can move with being applied to the similar principle of organic light-emitting device principle, even in the organic electronic devices that comprises organic solar batteries, organic photoconductor and organic transistor etc., moves.
Therefore, described organic electronic devices is optional from organic luminescent device, organophosphorus optical device, organic solar batteries, organic photoconductor (OPC) and organic transistor.
[preferred forms]
Below, provide preferred embodiment to understand better the present invention.But following examples are only for task of explanation, protection scope of the present invention is limited to this never in any form.
< embodiment >
The compound that < Preparation Example 1> preparation is represented by formula 1-2
Figure BDA0000437024830000141
prepare structural formula 1-2A
2'-aminoacetophenone (9.6mL, 80mmol) and phenylhydrazine (15g, 103.7mmol) are dropped in ethanol (100mL) and glacial acetic acid (30mL) and mixture is heated 5 hours while stirring.Mixture is cooled to normal temperature, filters the solid making and wash with ethanol (30mL), then vacuum-drying is to obtain structural formula 1-2A(14g, yield 83%).
MS:[M+H] +=226
prepare structural formula 1-2B
Vanadium Pentoxide in FLAKES (8.4g, 58.7mmol) is dropped in methanesulfonic (100mL) and mixture is stirred to Vanadium Pentoxide in FLAKES at 80 ℃ and dissolve completely.By structural formula 1-2A(6.3g, 28mmol) slowly add wherein, then mixture stirred 3 hours at 90 ℃ and be cooled to normal temperature.Reaction soln is dropped in aqueous sodium hydroxide solution at 0 ℃, mixture is stirred 10 minutes, then filter the solid making.Solid with distilled water wash vacuum-drying to obtain structural formula 1-2B(4g, yield 69%).
MS:[M+H] +=209
prepare structural formula 1-2C
By structural formula 1-2B(4g, 19.2mmol) and 4-chloro-benzoyl chloride (2.4mL, 19.2mmol) drop in tosic acid (50mL) and mixture heated 5 hours while stirring.Mixture is cooled to 50 ℃, then 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (4.8g, 21.1mmol) is slowly added wherein.Mixture is heated 2 hours while stirring, be then cooled to normal temperature, and wet chemical is slowly added wherein.Mixture is stirred to 30min, remove water layer, filter the solid obtaining.Filtered solid in trichloromethane recrystallization to obtain structural formula 1-2C(5g, 79%).
MS:[M+H] +=328
prepare structural formula 1-2D
By structural formula 1-2C (13g, 40mmol), connection boric acid pinacol ester (bis (pinacolato) diboron) (12g, 47mmol) and potassium acetate (12g, 118mmol) are dissolved in dioxane (150mL), mixture is heated to 50 ℃, by Pd (DBA) 2(0.23g, 0.4mmol) and P (Cy) 3(0.22g, 0.8mmol) adds wherein, and the mixture obtaining is heated 12 hours while stirring.Reaction soln is cooled to room temperature, distilled water (100mL) is added wherein, and extract mixture with methylene dichloride (100mL * 3).Organic layer is concentrated and is used ethyl alcohol recrystallization to obtain structural formula 1-2D(14g, yield 90%).
MS:[M+H] +=420
prepare structural formula 1-2E
Dibromobenzene (20g, 85mmol) is dissolved in tetrahydrofuran (THF) (100ml), then mixture is cooled to 78 ℃.By n-BuLi(2.5M, 37ml, 93mmol) slowly splash into wherein, then the mixture obtaining is stirred 30 minutes.Chloro diphenylphosphine (17g, 76mmol) is slowly splashed into wherein, mixture is stirred 3 hours and is heated to normal temperature, the mixture that then water (100ml) is added wherein and obtain with tetrahydrofuran (THF) extraction.Organic layer is concentrated and is used hexane recrystallization to obtain structural formula 1-2E(20g, yield 70%).
MS:[M+H] +=342
prepare structural formula 1-2F
By structural formula 1-2E(20g, 58mmol) be dissolved in trichloromethane (200ml), superoxol (20ml) is added wherein, then the mixture obtaining is stirred 12 hours.Add wherein MgSO 4and stir the mixture with except anhydrating, to the mixture obtaining filter, concentrated and with hexane recrystallization to obtain structural formula 1-2F(18g, yield 85%).
MS:[M+H] +=358
preparation formula 1-2
By structural formula 1-2D(9.4g, 22.4mmol) and structural formula 1-2F(8g, 22.4mmol) be heated to be dissolved in completely in tetrahydrofuran (THF) (200ml), then the wet chemical of 100ml2M is added in described solution, add wherein Pd (PPh 3) 4(0.26g, 0.22mmol), and mixture is stirred 12 hours.Mixture is cooled to normal temperature, removes water layer, and filter the solid making.Filtered solid with tetrahydrofuran (THF) and acetone recrystallization to obtain formula 1-2(8g, yield 62%).
MS:[M+H] +=572
The compound that < Preparation Example 2> preparation is represented by formula 1-4
Figure BDA0000437024830000161
prepare structural formula 1-4C
Structural formula 1-4C obtains in the identical mode of the preparation method with structural formula 1-2C, and difference is, with 3-chloro-benzoyl chloride, replaces 4-chloro-benzoyl chloride.
MS:[M+H] +=328
prepare structural formula 1-4D
Structural formula 1-4D obtains in the identical mode of the preparation method with structural formula 1-2D, and difference is, with structural formula 1-4C, replaces structural formula 1-2C.
MS:[M+H] +=420
prepare structural formula 1-4E
Structural formula 1-4E obtains in the identical mode of the preparation method with structural formula 1-2E, and difference is, with 2,6-dibromine naphthalene, replaces Isosorbide-5-Nitrae-dibromobenzene.
MS:[M+H] +=392
prepare structural formula 1-4F
Structural formula 1-4F obtains in the identical mode of the preparation method with structural formula 1-2F, and difference is, with structural formula 1-4E, replaces structural formula 1-2E.
MS:[M+H] +=408
preparation formula 1-4
Formula 1-4 obtains in the identical mode of the preparation method with formula 1-2, and difference is, replaces structural formula 1-2D and structural formula 1-2F respectively with structural formula 1-4D and structural formula 1-4F.
MS:[M+H] +=622
The compound that < Preparation Example 3> preparation is represented by formula 1-7
Figure BDA0000437024830000171
Figure BDA0000437024830000181
prepare structural formula 1-7A
Structural formula 1-7A obtains in the identical mode of the preparation method with structural formula 1-2A, and difference is, with 2'-amino-5-chloro-acetophenone, replaces 2'-aminoacetophenone.
MS:[M+H] +=260
prepare structural formula 1-7B
Structural formula 1-7B obtains in the identical mode of the preparation method with structural formula 1-2B, and difference is, with structural formula 1-7A, replaces structural formula 1-2A.
MS:[M+H] +=243
prepare structural formula 1-7C
Structural formula 1-7C obtains in the identical mode of the preparation method with structural formula 1-2C, and difference is, with Benzoyl chloride, replaces 4-chloro-benzoyl chloride.
MS:[M+H] +=329
prepare structural formula 1-7D
Structural formula 1-7D obtains in the identical mode of the preparation method with structural formula 1-2D, and difference is, with structural formula 1-7C, replaces structural formula 1-2C.
MS:[M+H] +=421
prepare structural formula 1-7E
By structural formula 1-2F(8g, 22.4mmol) and 4-hydroxy phenyl boric acid (3.1g, 22.4mmol) be heated to it and be dissolved in completely in tetrahydrofuran (THF) (200ml), then the wet chemical of 100ml2M is added in described solution, add wherein Pd (PPh 3) 4(0.26g, 0.22mmol), and mixture is stirred 12 hours.Mixture is cooled to normal temperature, and extraction organic layer, then will desolventize the solid filtering making by steaming.Filtered solid with tetrahydrofuran (THF) and hexane recrystallization to obtain structural formula 1-7E(7g, yield 84%).
MS:[M+H] +=371
prepare structural formula 1-7F
By structural formula 1-7E(7g, 18.9mmol) be dissolved in acetonitrile (200ml), the wet chemical of crossing chlorobutane SULPHURYL CHLORIDE (2.9g, 20.8mmol) and 100ml2M is added wherein and heating, then mixture is stirred 12 hours.Mixture is cooled to normal temperature, and extraction organic layer, then will desolventize the solid filtering making by steaming.Filtered solid with trichloromethane and hexane recrystallization to obtain structural formula 1-7F(9.5g, yield 75%).
MS:[M+H] +=653
preparation formula 1-7
Formula 1-7 obtains in the identical mode of the preparation method with formula 1-2, and difference is, replaces structural formula 1-2D and structural formula 1-2F respectively with structural formula 1-7D and structural formula 1-7F.
MS:[M+H] +=648
The compound that < Preparation Example 4> preparation is represented by formula 1-24
Figure BDA0000437024830000201
prepare structural formula 1-24A
Structural formula 1-24A obtains in the identical mode of the preparation method with structural formula 1-7C, and difference is, with 4-chloro-benzoyl chloride, replaces Benzoyl chloride.
MS:[M+H] +=363
prepare structural formula 1-24B
Structural formula 1-24B obtains in the identical mode of the preparation method with structural formula 1-7D, and difference is, with structural formula 1-24A, replaces structural formula 1-7C.
MS:[M+H] +=547
preparation formula 1-24
Formula 1-24 obtains in the identical mode of the preparation method with formula 1-2, and difference is, with structural formula 1-24B, replaces structural formula 1-2D.
MS:[M+H] +=848
< embodiment 1>
By substrate of glass (healthy and free from worry (corning) 7059 glass)---on it, be coated with one deck
Figure BDA0000437024830000202
Figure BDA0000437024830000203
thick ITO(tin indium oxide) to form thin film---put into the distilled water that is dissolved with dispersion agent, then use ultrasonic washing.The product of being produced by Fischer Co., as washing composition, is filtered the strainer of producing by Millipore Co. to the distilled water of twice as distilled water.To ITO washing, after 30 minutes, use distilled water to carry out twice supersound washing, totally 10 minutes.After using distilled water wash to complete, with Virahol, acetone and methanol solvate, carry out supersound washing successively, be then dried.
By six nitrile six azepine benzophenanthrenes, by heating on transparent ITO electrode, vacuum moulding machine is
Figure BDA0000437024830000204
thickness, so prepares electrode to form hole injection layer.By NPB
Figure BDA0000437024830000205
---its material that is a kind of transporting holes---vacuum moulding machine thereon, and by the compound vacuum moulding machine of the compound of main body H1 and adulterate body D1 is
Figure BDA0000437024830000206
thickness is as luminescent layer.Then, by the compound of formula 1-2 synthetic in Preparation Example 1 and LIQ, by heating, vacuum moulding machine is (extremely thickness) be electronic injection and transport layer.Organic luminescent device has by making
Figure BDA0000437024830000212
the quinoline lithium (LiQ) of thickness and having
Figure BDA0000437024830000213
the aluminium of thickness is deposited on successively on electron transfer layer and manufactures to form negative electrode.
Comparative example by E1 as electron transfer layer.
In above-mentioned steps, the sedimentation rate of organic materials remains on
Figure BDA0000437024830000214
and the sedimentation rate of quinoline lithium and aluminium remains on respectively
Figure BDA0000437024830000215
with extremely
Figure BDA0000437024830000217
Figure BDA0000437024830000218
< embodiment 2>
In the mode identical with embodiment 1, test, difference is, with formula 1-4, replaces formula 1-2 as electron transfer layer.
< embodiment 3>
In the mode identical with embodiment 1, test, difference is, with formula 1-7, replaces formula 1-2 as electron transfer layer.
< embodiment 4>
In the mode identical with embodiment 1, test, difference is, with formula 1-24, replaces formula 1-2 as electron transfer layer.
< comparative example 1>
In the mode identical with embodiment 1, test, difference is, with E1, replaces formula 1-2 as electron transfer layer.
In this embodiment, on the organic luminescent device by each compound is prepared as hole transport layer material, test the resulting table 1 that the results are shown in.
[table 1]
Figure BDA0000437024830000221
As shown in the results, new compound of the present invention can be used as by introducing multiple substituting group etc. the material of the organic material layer that comprises organic light-emitting device organic electronic devices.The compound being represented by formula 1 of the present invention shows excellent performance as the organic light-emitting device organic electronic devices that comprises of the material of organic material layer at aspects such as efficiency, driving voltage, time limit of service.

Claims (8)

1. the compound being represented by following formula 1:
[formula 1]
Figure FDA0000437024820000011
Wherein
At least one in R1 to R9 represented by following formula 2 and all the other are hydrogen; Deuterium; Halogen group; Itrile group; Nitro; Hydroxyl; Replace or unsubstituted cycloalkyl; Replace or unsubstituted alkoxyl group; Replace or unsubstituted aryloxy; Replace or unsubstituted alkyl sulfenyl; Replace or unsubstituted artyl sulfo; Replace or unsubstituted alkyl sulphinyl; Replace or unsubstituted aryl sulfonyl kia; Replace or unsubstituted thiazolinyl; Replace or unsubstituted silyl; Replace or unsubstituted boryl; Replace or unsubstituted alkylamino; Replace or unsubstituted aryl alkyl amino; Replace or unsubstituted virtue amino; Replace or unsubstituted assorted virtue amino; Replace or unsubstituted aryl; Replace or unsubstituted fluorenyl; Replace or unsubstituted carbazyl; Or replacement or the unsubstituted heterocyclic radical containing one or more N, O and S atom;
[formula 2]
Figure FDA0000437024820000012
L is direct bond; Replace or unsubstituted arylidene; Or replacement or the unsubstituted inferior heteroaryl containing one or more N, O and S atom,
Ar1 and Ar2 are independently of one another for replacing or unsubstituted aryl; Or replacement or the unsubstituted heterocyclic radical containing one or more N, O and S atom, and
A is O, S or Se.
2. the compound of claim 1, wherein, the R5 in formula 1 is represented by formula 2.
3. the compound of claim 1, wherein, the compound being represented by formula 1 is represented by any one of following formula:
Figure FDA0000437024820000031
Figure FDA0000437024820000041
4. an organic electronic devices, comprising:
The first electrode;
The second electrode;
With one or more layers is placed in the organic material layer between described the first electrode and described the second electrode,
Wherein, the compound being represented by formula 1 that one or more layers in described organic material layer comprises any one in claim 1-3.
5. the organic electronic devices of claim 4, wherein, described organic material layer comprises one or more layers hole injection layer, hole transmission layer and injects and the layer of transporting holes simultaneously, and one or more layers in described layer comprises the compound being represented by formula 1.
6. the organic electronic devices of claim 4, wherein, described organic material layer comprises luminescent layer, and described luminescent layer comprises the compound being represented by formula 1.
7. the organic electronic devices of claim 4, wherein, described organic material layer comprises one or more layers electron transfer layer, electron injecting layer and transmits simultaneously and inject the layer of electronics, and one or more layers in described layer comprises the compound being represented by formula 1.
8. the organic electronic devices of claim 4, wherein, described organic electronic devices is selected from organic luminescent device, organophosphorus optical device, organic solar batteries, organic photoconductor (OPC) and organic transistor.
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